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Synthesis and rearrangement of 4-imino-4H-3,1-benzoxazines

Synthese und Umlagerung von 4-Imino-4H-3,1-benzoxazinen


N-Acylanthranilamides react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 4-imino-4H-3,1-benzoxazines in good yields. If the reaction is carried out without acid acceptor, N-acetylanthranilamides yield 2-methyl-4-quinazolones, whereas N-benzoylanthranilamides give 2-phenyl-4-imino-4H-3,1-benzoxazines. It has also been found that 2-methyl-4-imino-4H-3,1-benzoxazines rearrange under the influence of HCl or HBr into the respective 2-methyl-4-quinazolones; 2-phenyl-4-imino-4H-3,1-benzoxazines, however, do not undergo such a rearrangement.


Die Umsetzung von N-Acyl-anthranilsäure-amiden mit Triphenyldibromphosphoran in Gegenwart von Triethylamin als HBr-Akzeptor führt mit guten Ausbeuten zu 4-Imino-4H-3,1-benzoxazinen. Wird die Reaktion ohne säurebindendes Mittel durchgeführt, dann entstehen aus N-Acetyl-anthranilsäure-amiden 2-Methylchinazolone-4, jedoch erhält man aus N-Benzoylanthranilsäure-amiden 2-Phenyl-4-imino-4H-3,1-benzoxazine. 2-Methyl-4-imino-4H-3,1-benzoxazine erleiden unter dem Einfluß von HBr oder HCl eine Umlagerung in entsprechende 2-Methylchinazolone-4, während 2-Phenyl-4-imino-4H-3,1-benzoxazine zu einer solchen Umlagerung nicht befähigt sind.

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Mazurkiewicz, R. Synthesis and rearrangement of 4-imino-4H-3,1-benzoxazines. Monatsh Chem 120, 973–980 (1989).

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  • 4-Imino-4H-3,1-benzoxazines
  • Synthesis
  • Rearrangement
  • 4-Quinazolones